Iodo benzene diacetate → Bis(1-methoxy-2,2,6,6-tetramethylpiperidin-4-yl) Azodicarboxylate

HRID 129960

Reaction equation

HRID 129960 reaction equation
[NH:1]([C:18]([O:20][CH:21]1[CH2:26][C:25]([CH3:28])([CH3:27])[N:24]([O:29][CH3:30])[C:23]([CH3:32])([CH3:31])[CH2:22]1)=[O:19])[NH:2][C:3]([O:5][CH:6]1[CH2:11][C:10]([CH3:13])([CH3:12])[N:9]([O:14][CH3:15])[C:8]([CH3:17])([CH3:16])[CH2:7]1)=[O:4].C(O)(=O)C.C(O)(=O)C.IC1C=CC=CC=1>C(Cl)Cl>[N:2]([C:3]([O:5][CH:6]1[CH2:11][C:10]([CH3:13])([CH3:12])[N:9]([O:14][CH3:15])[C:8]([CH3:17])([CH3:16])[CH2:7]1)=[O:4])=[N:1][C:18]([O:20][CH:21]1[CH2:22][C:23]([CH3:31])([CH3:32])[N:24]([O:29][CH3:30])[C:25]([CH3:28])([CH3:27])[CH2:26]1)=[O:19]

Participants

4

Reactant 2

HCID 12217721Iodo benzene diacetateHCID 54536773Bis(1-methoxy-2,2,6,6-tetramethylpiperidin-4-yl) Hydrazine-1,2-dicarboxylate

Product 1

HCID 54025229Bis(1-methoxy-2,2,6,6-tetramethylpiperidin-4-yl) AzodicarboxylateYield 113.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 8.2 g of bis(1-methoxy-2,2,6,6-tetramethylpiperidin-4-yl) hydrazine-1,2-dicarboxylate, as prepared in Example 1, in 100 mL of methylene chloride is added 6.3 g of iodobenzene diacetate in one portion at room temperature. After stirring at room temperature for 50 minutes, the solution is washed with a 10% solution of sodium carbonate and then with brine, and dried over anhydrous magnesium sulfate. The dried solution is then evaporated to leave 9.3 g of the desired product. Recrystallization of the crude product from acetonitrile affords 6.5 g of the title compound; mp 145°-147° C.

Workup

  1. washthe solution is washed with a 10% solution of sodium carbonate
  2. dry with materialwith brine, and dried over anhydrous magnesium sulfate
  3. customThe dried solution is then evaporated

Sources & evidence

ORD record
ord-17f9d58fcc07419ab02ac8287a320651
Source dataset
uspto-grants-1995_11
Patent number
US05470980

Linked notes

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